2-Nitrobenzenesulfonyl chloride → N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-2-nitrobenzenesulfonamide

HRID 1852501Notes

Reaction equation

HRID 1852501 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]3[C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[CH:23]=[CH:24][C:9]2=3)=[CH:4][CH:3]=1.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35])([O-:27])=[O:26]>N1C=CC=CC=1>[O:16]=[C:12]1[NH:11][C:10]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=3[CH:23]=[CH:24][C:9]=2[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N+:25]([O-:27])=[O:26])(=[O:35])=[O:36])=[CH:7][CH:6]=2)[C:14](=[O:15])[CH2:13]1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 866893185-(4-Aminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

Product 1

HCID 86689317N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-2-nitrobenzenesulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

5-(4-Aminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione (190 mg, 0.59 mmol) obtained in Example 10, o-nitrobenzenesulfonyl chloride (197 mg, 0.89 mmol), and dry pyridine (5 mL) were mixed. The mixture was stirred at 80° C. for 17 hours. Pyridine was removed by evaporation under reduced pressure. To the residue was added water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give the titled compound as pale yellow crystal (233 mg, yield 78%).

Workup

  1. customPyridine was removed by evaporation under reduced pressure
  2. additionTo the residue was added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with dilute hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-8d7606c8918c48d589c27afb279b90d0
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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